Potassium Phosphate, Tribasic → 1-Benzothiazol-6-yl-3-(4-dimethoxymethyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80236

Reaction equation

HRID 80236 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][NH:12][C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.Br[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][C:22]=1[CH:23]([O:26][CH3:27])[O:24][CH3:25].CNC1CCCCC1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(Cl)(Cl)Cl.[Cu](I)I.CO.O1CCOCC1>[S:1]1[C:5]2[CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][N:12]([C:21]4[CH:20]=[N:19][CH:18]=[CH:17][C:22]=4[CH:23]([O:26][CH3:27])[O:24][CH3:25])[C:11]3=[O:15])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 207151453-Bromo-4-(dimethoxymethyl)pyridineHCID 666785541-Benzothiazol-6-yl-imidazolidin-2-one

Product 1

HCID 498724521-Benzothiazol-6-yl-3-(4-dimethoxymethyl-pyridin-3-yl)-imidazolidin-2-oneYield 52.9%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 887MethanolSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

Using the same reaction conditions and work up as described in Example 1, step-3,1-benzothiazol-6-yl-imidazolidin-2-one (I-84b: 515 mg, 2.35 mmol) was refluxed with 3-bromo-4-dimethoxymethyl-pyridine (600 mg, 2.584 mmol), copper iodide (44.7 mg, 0.2312 mmol), N,N′-dimethyl-cyclohexane-1,2-diamine (80.8 mg, 0.7405 mmol), potassium phosphate (1.4 g, 7.046 mmol) and 1,4-dioxane (20 mL) at 110° C. for 12 hours to afford the crude product. The reaction was monitored by TLC (10% MeOH in chloroform). Purification by column chromatography on silica gel (2% methanol in chloroform) afforded 460 mg of the product (52.9% yield).

Workup

  1. customthe same reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (2% methanol in chloroform)

Sources & evidence

ORD record
ord-9528f764c4114816a73e1d2b7b3500d0
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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